


Resignation and Redemption

by The_seal_is_for_marksmanship



Category: Supernatural
Genre: Confused Castiel, Crowley Being an Asshole, Dean Being an Idiot, M/M, Protective Crowley, Slavery, Torture
Language: English
Status: Completed
Published: 2017-09-06
Updated: 2017-10-24
Packaged: 2018-12-24 11:31:50
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 19
Words: 14,318
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12011829
Author URL: https://archiveofourown.org/users/The_seal_is_for_marksmanship/pseuds/The_seal_is_for_marksmanship
Summary: AU after Season 7, Episode 1 - Crowley takes his revenge on Castiel's purgatory betrayal by kidnapping Cas.  To protect Dean, Castiel swears his eternal servitude to the King of Hell, and a begrudging friendship eventually develops between the angel and his captor. After months of getting to know Crowley, Castiel catches back up with Dean, and the angel must choose between the eldest Winchester or the King of the Crossroads.





	1. Chapter 1

**Author's Note:**

> Okay, so brief note. I started writing this story back before Season 7. I had this grand plan to finish writing before Season 7 began but graduate school got in the way. So it's finally done. Well mostly done. I have a smut scene I still have to finish but the story itself is complete. So no worries if you start reading this - this story will have a conclusion. And if all goes well a smut scene. I'll likely post a couple chapters at a time, and should be posting once or twice a week at least.
> 
> So I mention this for a few reasons. One, because sometimes the tone from one chapter to another is not precisely the same. I tried to match, but it's been years in-between some chapters. And two, I mentioned it because it took so long to write I had to make it an AU. So it's AU after the first episode of Season 7.
> 
> Thanks for pink_bagels at Livejournal for the edits. It's been so long ago she probably doesn't remember, but she gave me some feedback that really helped me write the story. 
> 
> Oh, and finally, if you like this story please let me know. I'm thinking about expanding it into a series of stories, so if you'd have any interest in that please let me know. And thanks for reading!

Castiel forced his bright blue eyes open and tried to focus, but his head was so foggy and his eyes so blurry he jammed his lids shut again before he could figure out where he was. He closed his eyes for a few seconds to settle the throbbing in his head, took a deep breath, and started again.

A few rapid blinks brought the room into clear view. There wasn’t much to see: it was a small bunker of some kind, with a concrete floor and yellow tile walls and ceiling. A few piles of what looked like construction material were scattered across the room, but Castiel could see no signs as to what this place was used for. There were no windows. Castiel did not like that. 

A quick check of his body sent back more worrying signs. He was sitting on a rough metal chair that was cutting into his back, and an attempt to adjust his frame to get more comfortable let him know he was tightly bound to the chair. His hands were roughly shackled behind him, and chains held his ankles, thighs, abdomen, and shoulders to the seat. Even more troubling was the fact that he could feel his wings out, uncomfortably maneuvered so that they came out behind his back through the space between the chains that held his abdomen and shoulders taut. His wings were incredibly sore and shockingly cold, the tips of his blue-black feathers brushing against the concrete floor and absorbing the frigidness of the ground below him.

Castiel struggled, but knew it would be in vain. He could feel the strength of the chains that held him and sense the whisper of binding power across his whole being, indicating that the chains must be covered in Enochian runes. A closer examination of the bindings confirmed his theory. The angel was completely, thoroughly, irrevocably trapped.

A swift movement of air warned him of another presence in the space. Before he could whip around to see who was there, a blinding pain shot through his scalp as his captor grabbed a handful of his dark hair and yanked cruelly. His head was roughly forced up to look in the eyes of the man who had stolen him away and taken him here.

“Hello luv,” said Crowley, a smirk playing across his face. “Miss me?”


	2. Chapter 2

Oh my. If Crowley could bottle up the look on Castiel’s face, he’d drink that every day instead of his Craig. Hate, anger, and downright terror all mixed together on the angel of the Lord’s face - delicious.

“You must’ve known this day would come. A little old angel like you screws over the King of bloody Hell and you think you’ll get away with it? Come on. That’s just a little too optimistic.”

Castiel looked confused. “How did you capture me demon?”

“Oh, simple really. Found you while you were spying on your true love, Dean Winchester, and hit you upside the noggin with a pipe covered in Enochian symbols. Then I took you here and trussed you up all nice and tight with some powerful Enochian chains that take away your angel mojo and make you as feeble as a human. I even used an old spell I found to bring your wings out for good measure. You’re mine kitten. You picked the wrong demon to mess with.”

“But you sided with Raphael.” Castiel added lamely.

“Because you’re a traitor! Because the angel I originally had a deal with went and stole all the souls we were set to split! No other choice mate. But really, did you enjoy it? How’d you like playing God Cas?”

Castiel was quiet for a second, thoughtful. “I was arrogant and prideful. I believed I was chosen to lead the world in my Father’s absence. I was mistaken. But I could not give the souls to you. You would have…”

Crowley cut him off. “What, would have killed? Would have enslaved? Would have made the earth into what I wanted it to be? Seems you took care of that for me, didn’t you?”

Castiel’s face softened. “I never meant…I thought it was what I was meant to do…”

“Like God would make you king? You’ve got more balls then brains angel. And you would have gotten away with it too, if it wasn’t for those meddling Winchesters.” Crowley laughed. “Had to rely on Dean and Sasquatch to save the world yet again. Lucky they got the Leviathans back into Purgatory before your little stunt could cause any more damage.”

Crowley leaned down so his face was only a few inches from the angel's. “Speaking of the Hardy Boys, how’d they react to you being back? Did they welcome your return with open arms? I bet they didn’t. I bet they just hate you.”

Castiel looked into Crowley’s eyes with a fire that he could tell was forced. “The Winchesters will come to forgive me. They are good men. They are my friends.”

Crowley’s head shot up, and he laughed so fully his whole body shook. “Forgive you? Really now, that’s more optimistic than thinking that I would never come and find you to take my anger out of your angelic arse. Forgive you? Let me guess, the only time you’ve seen them since they sent the souls back is when you’ve been spying on them?” Castiel’s silence gave Crowley his answer. “This is rich. They’ll forgive you? They never want to see you again Cas. You screwed them over royal. Must say I’m proud of just how much pain you caused the both of them. They have always been such a thorn in my side.” 

Castiel stared defensively at Crowley, but he couldn’t hold his gaze for long. “They will forgive me Crowley.” Castiel insisted. “Friends forgive one another.”

“If they were willing to forgive you, I wouldn’t have caught you. Instead of me sneaking up on you while you were playing peeping Tom, you would have been safe in a hotel room, helping Dean and flannel shirt solve whatever case they are too incompetent to work on their own. But they are so ashamed of you they would rather just bumble about and possibly get themselves killed then call you in for help. And who wouldn’t be mortified to be seen with you? You, the angel who declared himself god and wasn’t qualified to lead a Girl Scout troop? That poor, awkward seraph who was given great power and used it to threaten to kill his only friends? And they’re going to forgive you? Castiel, they’re going to curse your name until their last breaths.”

Tears shone in Cas’ eyes. Oh, this was too much.

“I never…I never meant to hurt them.” Castiel whimpered.

“Oh but you did. You ruined Sam. Has Lucifer greeting him every morning with nice little visions of hell. And Dean? Poor Dean, with all his trust issues, finally made a friend to have said winged friend stab him in the back. That poor sod can’t even function anymore without a buzz.” 

Tears were falling openly now from the angel’s face, and small sobs were escaping his mouth. “Do your worst demon. I deserve it.”

“I will do my worst. I’ll cut and maim and…wait, hold on. You want me to?” Crowley pondered. This had never happened before. “You can’t seriously be fine with me cutting you to ribbons.”

The angel blinked away his tears, but his chest was still hitching up and down from silent sobs. “I want you to. I am nothing. I don’t deserve to breathe. I have nothing to live for. Do your worst demon. It can be no more terrible then what I have done to myself.”

Well, that was a challenge if Crowley ever heard one. And he had certainly never had anyone acquiesce to being tortured before. This could be interesting. “Alrighty luv. Let’s see if I can make you regret what you just said.” The demon grabbed a handful of Castiel’s feathers and pulled. “Let the games begin!”


	3. Chapter 3

Castiel couldn’t remember how long he had been here with Crowley. He was guessing weeks, but each day bled into another like he bled out onto the concrete floor. The demon wasn’t gentle, but Castiel didn’t care. There was nothing in this world worth caring about as it pertained to him.

Yes, he had been angry when Crowley had first taken him. But then, as the King of Hell spoke about the damage Castiel had caused during his stint as God, and the myriad of sins he had broken in his blasphemy, well, truthfully, Castiel was glad for Crowley’s revenge. He hadn’t expected such an emotional response to Crowley’s goading to be honest, for Castiel was never an emotional angel. But whether it was the spell in the chains reducing his angelic powers, the trauma from his Leviathan possession, or simply guilt from the horrors he inflicted on those he loved the most, Castiel was wrought with grief as Crowley laid out his sins against the Winchesters. 

Dean. Oh God, Dean. What had he done? What he had done to Sam was enough to be certain that he would be damned to hell once he died, but what he did to Dean? No hell could be worse than knowing he had broken the most beautiful of souls.

He had loved Dean once. He had wanted to “know” him in all ways, even in the Biblical sense of the word. To feel and cherish him like no one had before. He had never felt so close to any being, never wanted to have relations with another. But Dean. Oh Dean.

The thought of hurting the only man he had ever loved shamed Castiel so much that he was often inside his head during torture, reliving the pain he caused Sam and Dean. Castiel’s emotional distress was so great he often didn't noticed the physical torture Crowley inflicted upon him.

So the angel never cried out in pain as Crowley broke his bones with a sledgehammer, never whimpered as the demon used a saw to separate hand from arm, foot from leg. Crowley’s tortures weren’t pain. Pain was knowing that he deserved this, that what he felt was nothing like what Dean or Sam were going through. He knew as time passed that the King of Hell was becoming frustrated with Castiel’s lack of reaction, and he was sorry to disappoint him. But he was broken already. Breaking him apart with silver and bullets wasn’t going to change a thing.


	4. Chapter 4

“Maybe I can invite dear old Dean to our little soiree?” Crowley asked.

Castiel’s glazed over eyes suddenly blazed blue, his head jerked back as if he had been slapped, and his face flushed red. Interesting reaction.

“What…what did you say demon?”

“I said we could invite Dean to join us. I mean, you’ve been quite dull, and the Winchesters always seem to liven you up a bit. I’d invite the moose, but since Luci is fiddling around in that noggin of his he seems a bit predisposed. But Dean…well, Dean would be lovely, don’t you think? I can set him up in a chair right across from you and you can watch. Hell, maybe later he can break and help me torture you. Hear he’s right handy with a knife. Sounds like it’ll be a bit more fun than watching you space out all day.”

Castiel looked wrecked. “Please,” he breathed. “Please, don’t. Whatever you want from me, I’ll do it. Leave him out of this.”

“Begging now? That’s a bit of a different route for you, isn’t it?”

Castiel closed his eyes as if he were in pain, but Crowley had stopped cutting into him as soon as he had mentioned Dean so he doubted that was the reason behind Cas’ reaction. “I betrayed him. I ruined him. I can never fix that.” Castiel’s eyes flew open and settled on Crowley with a puppy dog look that would have given Sam a run for his money. “But I am begging you, do not bring him here. Do not make him suffer any more pain by my actions. I deserve this. He does not.”

Crowley wasn’t surprised the angel was throwing himself on the fire for Dean once again, but he didn’t expect to get this much emotion out of Castiel. After weeks of nothing after agonizing torture, to finally have Castiel pleading for Crowley to have mercy - not for himself, but for Dean Winchester - was a bit of a surprise.

Crowley leaned low, his silken tie brushing against Cas’ chest as he brought himself close to the angel’s ear. “And what would you give me to leave him alone?” He whispered.

“Anything. Everything,” Castiel said, in a voice that crackled with desperation and fear.

“Even your grace?” Crowley asked.

Castiel hesitated, but only for a moment, barely long enough for Crowley to even register the pause. “Yes, even my grace.”


	5. Chapter 5

“But see, problem is angel, I could have your grace in a moment. I own you. I could break that pretty face of yours into pieces so fine you wouldn’t have bones anymore. I could cut you open and play Operation with your organs. Hell, I could be balls deep in your sweet ass before you could blink.” Crowley leaned low to whisper in Castiel’s ear, and the angel could smell scotch and sulfur in the scent of the demon. “You have nothing to offer me.”

Castiel was desperate. The demon would bring Dean into this, he had no doubt. He was a fool for reacting so strongly to the goading of Crowley, and his inability to keep his emotions in check could bring even more pain to a person he had already greatly hurt. He must stop the demon. 

Castiel pulled sharply on his bindings in desperation, hoping against all hope that this time he might be able to break free. Crowley laughed at the angel’s useless struggles. “Bollocks kitten. Still trying to escape? Really now. You’re embarrassing yourself.”

Castiel stopped. He knew that Crowley was right, that there was really no way out. He was fine with that if it only affected him. He was nothing. But Dean…there had to be something…

“You can use my help Crowley. You cannot torture aid out of me. I have to be willing to serve you.”

The demon looked intrigued. Castiel knew he was on the right track. He might be able to save Dean after all.

“And what can you offer me angel? If you haven’t noticed, I’m kind of the King of Hell. No real need for a lowly ex-god.”

“I can read languages you cannot. I have knowledge of events that occurred thousands of years ago. I know the actions of angels, and I know how they work. I can kill demons with a touch.” Castiel was panting he was so desperate for this to work. “I can simply file papers or fill out forms or whatever you desire. I do not need sleep. I can serve you 24/7. And I will, if you will leave Dean, Sam, and Bobby alone.

Crowley looked pleased. “And how long with I have your servitude? Hmm? How long would I own you, in all senses of the word?”

“However long you need to own me to agree to protect the hunters.”

The demon looked like he had just received a fantastic present. Castiel thought that, in truth, he had. In one simple threat, Crowley had gone from having an angel carving canvas to having an unquestioning servant who he could still torture.

“Well luv, that’s an offer I just can’t refuse. Let me draw up the paperwork.”


	6. Chapter 6

“Oy, feathers! Get in here!”

Castiel sighed and set aside his book, a copy of the Rig Veda Crowley had gotten him a month ago because “you staring into space Castiel is creepy, and it needs to stop.” Consequently, Crowley found an entire volume of works for Castiel to occupy his time with, and the angel was devouring books when he wasn’t working for Crowley.

Castiel rose from his armchair in the living room and walked into the office of the medium-sized apartment that Crowley and Castiel stayed in. The room was tastefully decorated, with chocolate walls and deep green furniture, all smooth lines and polished surfaces. In the few months that Castiel had worked under the King of Hell, he had discovered how organized and together the demon was. His office simply reflected his personality.

Currently, however, the office looked like something had exploded in it. And judging from the smoke in the room and the fire that was smoldering over the mahogany desk top, Castiel would have to guess that something actually did.

The angel tilted his head and appraised the situation. “Has there been a mishap?”

Crowley looked up at Castiel, but had to wipe soot off his face to be able to actually make eye-contact with the angel. “Are you saying you didn’t hear that?”

“I must have been too absorbed in my reading to notice.”

“Really?” Crowley shook his head with disbelief. “You’re not much of a bodyguard.”

“I did not know that was in my description. I thought the hellhounds were adequate enough for that position.”

“I don’t think the hounds are good at checking mail for bombs, luv.”

Castiel walked forwards to inspect the desk. “Really? A mail bomb? How exactly was that supposed to overthrow you?”

“No idea. Not my area of expertise. You figure it out so I can run a flaming pike up the moron that decided to try and kill me with a letter bomb.” Crowley scanned the room in disgust. “Look what they did to the place! Look at the curtains! Beyond repair, I tell you!” Crowley continued to glance around, face pulled up in disgust. “And look what these wankers did to the rug! That rug was worth more than you, and it’s rubbish now! Demons! The whole lot of ‘em. Worthless, putrid monsters!” Crowley then took to stomping around the room and cursing in earnest fury.

Castiel could tell that beneath the agitation on the surface of Crowley’s behavior was a small amount of fear and even sadness. He could see it in the slumped shoulders of the demon, in his darkened eyes and his frazzled gait. Two assassination attempts had already occurred this month, and it seemed to finally be getting to the demon.

Castiel walked over and put his hand gently on Crowley’s shoulder in an attempt to sooth Crowley’s agitation. “It is alright. We will find whoever enacted this plan.”

Crowley stopped pacing, and turned to address the angel, face transitioning from a complex display of emotions to cold indifference. “I’ve got work to do. Find who did this.” And with a last look at the place, plus an angry whisper of “bloody curtains”, the King of Hell left the room.

Castiel began investigating as soon as the demon disappeared, eyes scanning earnestly over the office. As he explored the scene, the angel’s mind began to wander, and his brain began thinking of what would have happened if Crowley had actually been hurt by this misguided assassination attempt. And surprisingly, Castiel found he would have been upset if the demon had been injured.

The thought made Castiel pause his examination of the office. What in the name of his Father would make him think that? Should he not be glad if his captor were to be killed?

In the beginning of his enslavement to Crowley, Castiel’s answer would have been a resounding “yes.” He hated signing the contract with the demon, had only done so to save Dean and his friends, and simply the thought of spending the rest of his life with the King of Hell had made him want to cease existing. The demon had spent the few minutes necessary for explaining the terms of the contract (“none of that bloody bitching if you don’t like what I say…fine, no killing innocents…laundry, yes, you have to fold it...”) with a smile on his face so large Castiel was sure it must have been painful. But the demon had bested him, broken him, and gotten his soul as a trophy. He had every right to gloat.

And the smile after he sealed the deal with a kiss - well, a crocodile’s grin was less dangerous.

And for a few weeks, things had been very bad. Crowley still would torture the angel, pulling out feathers and driving in knives while Castiel suffered silently in pain. And as he did before, he had to listen to Crowley go on and on about how Castiel had betrayed Dean. It was easier for Castiel to hear this time around because he had at least secured protection from Crowley for the hunter, but hearing it over and over still hurt. At night, Crowley would chain Castiel’s ankle to the wall in the living room, an act that both knew was unnecessary since Castiel would never attempt to escape, but something the demon did anyways to show Castiel exactly who was in charge. 

But things changed. Slowly and strangely, they changed. Crowley kept mostly to himself since he didn’t trust any demon as far as he could throw them, so oftentimes it was just him and Castiel in the apartment for hours at a time. And although they were both completely different in terms of morals, they were incredibly similar in brains and power.

In the past, when they were forced to converse on their hunt for purgatory, conversations were clipped and often hostile. Neither wanted to be in the partnership, so there was no chatting, just business (unless Crowley wanted to annoy Castiel – then the demon would talk about asinine subjects for hours on end.) But with this new, basically eternal, partnership between the pair, conversing had changed to something not actually too far removed from pleasant. Castiel was surprised as to how well-read the demon was, and even on issues where their opinions were vastly disparate, Castiel had to at least acknowledge that Crowley’s positions were always incredibly argued. They spoke together about literature, history, art – topics where Crowley’s hundreds of years, and Castiel’s thousands, of existence brought depths to the discussion that neither could find in conversations with others on the same issues. It had stunned both of them, but a friendship developed. Albeit, it was still a begrudging one, and Crowley still made the angel well aware of his subservient position to the King of Hell, but it was a friendship nonetheless.

The tortures tapered off, and then disappeared completely. In only a few short months, the two had become quite secure in their relationship with one another. Castiel worked whatever errands were needed to be done during the day - which could involve anything from killing a rebelling demon or vacuuming rugs - while Crowley completed his hell administrative duties. Then, in the evenings, both would sit down to a dinner neither needed to eat and chat. And after their meal, they would lounge around in the living room and read in comfortable silence until they decided to retire to their separate bedrooms. Each day was like this, but neither of them minded. 

And if Castiel was being honest, really honest, he would have to say that he was happy. Of course, he still missed his freedom and his friends, but what he had was simple and relatively carefree. He never participated in anything bad directly, and Crowley was probably the most just ruler of hell in thousands of years. It wasn’t bad at all to be working for Crowley. It was…nice. And Castiel had rarely had anything in his life before that was nice.

Castiel was brought back to reality with a snap. Nice? He could not think about this being nice. It was a dangerous road, becoming comfortable with a demon, and he should not travel down that path. He had a job to do. This was a business partnership.

Castiel saw something out of place out of the corner of his eye, and a smile spread across his face as he noticed a particle used for the explosive that wasn't destroyed in the blast. A simple tracking spell out of the grimoire Castiel read last week, and he would know who tried to kill Crowley before dinnertime. The King of Hell would be pleased. 

And the fact that Castiel was so happy that Crowley would be pleased shouldn’t be providing the angel with as much pleasure as it was.


	7. Chapter 7

It was dinnertime, and Crowley was looking forward to seeing Castiel. Crowley had spent most of the day in his office, completing paperwork and writing deals. He had given Castiel a list of books that he needed the angel to locate for a spell, so Crowley hadn't seen Castiel all day. It was kind of lonely to be honest. Although he'd never tell the angel that. 

He was starting to get a little soft when it came to the seraph. Ten months together, and now Crowley was used to having Castiel around. It was the kind of comfortable Crowley has always actively avoided. He certainly couldn't trust any other demon. Too many of them had tried to overthrow him, so he couldn't feel anything near trust towards any of hell's denizens. But this situation was different - Castiel was different. His loyalty was guaranteed because the angel wanted to protect the Winchesters. Crowley could trust that the angel wouldn't hurt him, and this trust was something Crowley valued. 

His desire for trust between he and the angel constantly disgusted him. 

Crowley met the angel in the dining room, but something was off. Castiel wouldn't look him in the eye, and every time that Crowley tried to get the angel to talk Castiel would answer him with one or two words. It was maddening.

"You've barely said a word all dinner Castiel." Crowley stated. 

Castiel looked up from the barely-eaten plate in front of him. "I'm sorry. I did not have much to say."

Crowley scoffed. "You're a terrible liar kitten."

"I am not." Castiel said with a scowl.

"You're as bad at lying as I am good at it. So what is it that's eating you? You're being incredibly dull, and I'm starting to get bored."

Castiel looked down at his plate with a sigh. "It's just today is important to me. It's the day I raised Dean from hell. I always liked to visit him on this day. But I'm fine."

Crowley hadn't know what to expect from his line of questioning, but this was a surprise to him. He remembered the day that he brought Dean out of hell? Crowley thought for a second it was kind of endearing, but then he remembered he was the king of hell and he was not to find anything endearing. But the angel looked so sad...

What would it hurt if he let the angel go see Dean? Perhaps his reputation, but maybe it was worth the risk if he could get the angel to smile.

"You have tonight. Just tonight. Then I don't want to hear another word about Dean friggin' Winchester." Crowley stated.

Castiel's stopped staring at his green beans and looked hopefully up at Crowley. "Really?"

"Yes, really. I can't stand you being this bloody boring. You have 'til dawn. Then you come back here and stop moping."

Castiel smiled widely, face beaming and nose crinkling in a way that Crowley definitely was not thinking was cute. "Crowley, thank..."

"If you say thank you I will puke," Crowley interrupted. "And I will make you clean it up. You better get going before I change my mind."

Castiel disappeared the moment that Crowley finished his sentence. Crowley went over and poured himself two fingers worth of scotch. He was starting to have some uncomfortable thoughts about the angel, and scotch was the best solution for that line of thinking. Drinking, he mused, might be enough to distract him from the fact that he is falling for a fallen angel.


	8. Chapter 8

**Notes for the Chapter:**

> Okay, so in this chapter Dean is an asshole. I love Dean as much as the next Supernatural fan, but he can be so hard on Castiel. I just cranked that up a little bit. Don't worry, they'll work on their issues in a later chapter.

Castiel appeared in Bobby’s den. He knew Dean would be here. He was always tracking   
Dean, always making sure he was safe. Castiel was constantly at the ready to come to the hunter’s aid if he got into trouble, but so far he had had no occasion to help. Crowley would likely be understanding if he one day disappeared to stand and fight for Dean, and even if he wasn’t, only Dean mattered – Castiel had long ago given up the idea that he himself was worth anything at all.

The hunter had fallen asleep in an armchair; his head was kicked back, mouth open and pooling with drool. Castiel hated to wake him, but he was afraid Crowley would change his mind and come to get him anytime, and he wished so strongly to speak to Dean.

He walked to where Dean was resting and laid an arm on his shoulder, hand covering the palm print he left on Dean so long ago. Dean awoke with a start and moved to grab for a knife. As he turned to focus on the person who had roused him, Dean halted his hunt for the blade and instead stared at Castiel, his eyes changing from wary to angry.

“What the fuck are you doing here?” Dean asked, bitterness dripping through every syllable.

Castiel had not expected a friendly greeting, but this reaction was much more hostile then he had dreamed it would be. “I’m sorry. I hated to wake you, but I do not have much time to talk.”

Dean laughed. “You think that I’m upset because you woke me up? I’m pissed off because it’s been ten months since I’ve seen you and, oh yeah, I heard you’re working with Crowley.”

Oh. Castiel had hoped that his involvement with the demon would be something Dean didn’t know. “It is not what you think Dean. I promise. I just can’t explain.” No matter what Castiel did, he would never tell Dean he had sold his freedom for the safety of the Winchesters and Bobby. Dean would feel guilty, and Castiel did not deserve anyone’s guilt or pity, especially not from someone he had so greatly betrayed.

“Of course. The angel that turned against his best friend, took over the world, and broke Sam’s mind just made a promise. I’m sure that’s worth something. Sorry Cas. I should just take your word on the whole thing.”

“Please,” Castiel pleaded. “You must understand. I am not working for him because I like him. I had no other choice.” Although being completely honest, he did not dislike the demon much anymore, but that was beyond the point.

“No other choice!” Dean screamed, moving forward toward the angel. “You had no other choice then to abandon your friends and work for a fucking demon! Really Cas. What the hell is wrong with you?”

Castiel opened his mouth to try and explain, but as his mind was trying to find the words Dean slammed his hand into Castiel’s chest and pushed the angel back into the wall. He held Castiel there roughly, his palm pressing so hard into Castiel’s sternum he thought he might bruise. “I don’t want to hear it Cas.” Dean’s head dropped, his shoulders slumping in defeat. “I just don’t. You, you’re dead to me. To Sam, to Bobby. You’re nothing to us anymore.”

“Dean,” Castiel whispered, tears welling up in his eyes. “You…you do not mean that. Please. Please say you don’t mean that.”

Dean’s head snapped up and he stared at Castiel, eyes cold and fierce. “I’ve never meant anything more in my life.”

A sob escaped Castiel’s throat as tears fell down his face. “I’m begging you. You don’t have to forgive me Dean. I have not earned your forgiveness and never will be able to. But please don’t disown me. Do not leave me alone.”

Dean released the pressure on Castiel’s chest and walked away. As he was leaving the room, he turned to Castiel. “Beg all you want Cas, but I won’t change my mind. You deserve to be alone.” Dean started walking out of the room, then added as an afterthought, “You come here again and I’ll kill you.”

Castiel watched Dean walk out of the room through tear-filled eyes. His body felt weak, his mind reeling and in agony from what Dean had said to him, his brain barely comprehending that he had just completely lost the man he loved more than anyone on this earth. His legs too wobbly to support him, the broken angel slid down the wall to rest on the floor where he huddled and sobbed until his throat was sore and his eyes were aching.


	9. Chapter 9

**Notes for the Chapter:**

> This chapter is definitely explicit. It's fine if you aren't interested in the explicit stuff and want to skip it - although this chapter does some character development you won't miss anything too important. Also, this is not the sexy scene I've been struggling to write. I'm hoping to finish that sometime this week so the story will actually be done.

God, nothing on this earth was more pathetic then a pining angel. Really, there was absolutely nothing that was more obnoxious. So yes, Crowley did allow the angel to go visit his lover Dean Winchester. It didn’t mean he was being nice. He honestly just couldn’t take that look of lost love on Castiel’s face for one more second. And anyways, it freed him up to drink a ridiculous amount of Scotch, watch some documentaries on Hitler, and hell, maybe even jerk off. That damn angel almost always was here, and it really was no fun to worry about the angel popping into the room while he was masturbating. Because of that, Crowley hadn’t gotten off for quite a while, and it was making him a bit tense.

_It’s not that you care if he walks in on you and sees you Crowley. It’s just that you’re worried he’ll realize it’s you you’re thinking about as you cum._

Crowley drained his full glass of Craig in one quick gulp. His subconscious was wrong and could take a flying leap for all he’s concerned. He doesn’t masturbate to the thought of Castiel. He doesn’t.

_Denial much? Because if I remember right, the last time you came was while thinking of that little angel servant of yours bound underneath you and moaning while you shoved your cock deep into his tight little…_

“Oh, fuck off,” Crowley said to no one in particular. “If I wanted him I could have him. I just don’t.”

_You want him to want it. That’s why you haven’t fucked his brains out. You want him to beg you for it. You want him to be willing to defile himself for you.”_

Why wasn’t he drunk already? What cruel joke was this? Crowley took another swig of Scotch from the neck of the bottle, hoping that just a little more alcohol would put him over the edge.

_He’s not here, you know. He won’t know. He won’t be back until sunup, and he’ll have no clue that you wanked it while thinking of those pouty lips of his sucking you off. Do it Crowley. You know you want to – hell, you know you need to._

Goddammit. He was so hard. This was ridiculous. All he wanted was a quiet evening at home, and now he’s got an erection so throbbing that’ll he’ll be utterly useless until he takes care of it. Sighing, Crowley unbuttoned his dress pants, pulled down the zipper, and took out his painfully hard dick.

He wanted to get this over with soon. If he was going to jerk off while thinking of the angel, well, so be it, but he wasn’t going to take his time about it. Crowley started off with a frantic pace, hand moving up and down the shaft quickly, his movement sped up by the precum leaking from his tip. His mind wandered, thinking of Castiel on all fours on the plush carpet of Crowley’s apartment, hair mussed and blue eyes closed in pleasure. Crowley would lean over him from behind, with one hand gripping the angel’s firm ass and the other pulling Cas’ chin towards him so he could place a kiss on his chapped, plump lips.

“Please Crowley,” the angel would plead. “Please, I beg of you. Do not tease me any longer.”

And Crowley would comply, lubing up his fingers and then moving them inside Castiel to open him up, the angel squirming underneath him as he’s struck by the pleasure and pain of having Crowley’s fingers inside him. Then, when the angel is panting and not able to form words, only moan, Crowley would insert his large cock into Cas, muscle clenching around flesh as both angel and demon moan at the sensation.

Oh God, Crowley was so close. His fist moved up and down his dick with a speed so quick it was almost painful. He could feel his orgasm building. Fuck, he was almost there…

And then an angel appeared on the rug before him.


	10. Chapter 10

“Bloody hell!” Crowley yelped, moving quickly to put his fun bits back into his pants. “What in fuck’s sake are you doing here? I thought you would be gone all night!” 

No response, just a whimper. What in the world?

“Oy, angel! You there, lying on the carpet! What is going on?”

More whimpering. Dammit.

Crowley decided to try a more gentle tactic, and moved slowly towards the crumpled angel. “Cas? Speak to me. What’s wrong?”

Only then did Castiel turn around, and what Crowley saw on his face was so sad that even the King of Hell felt bad for the poor thing. The angel’s eyes were red and swollen, his hair mussed, snot dripping out of his nose and tear stains running down his cheeks. Whatever remained of Crowley’s erection was gone in the instant he saw the devastation on Castiel’s face.

“Christ…” Crowley breathed. He took a moment to compose himself, and then moved down to sit beside Cas on the floor. Usually the angel hated for Crowley to be in his personal space, but this time he didn’t even flinch as Crowley sat down. Not a good sign at all.

“Look, I need you to tell me what happened.” 

“Dean.” It was barely a whisper, and the demon had to strain to hear it, but it was something.

“What about him? Is he alright?”

“HE’S fine.” 

“Then what is the bloody deal? I thought you wanted to see Dean.”

Silence.

“Fuck, I’m no good at this. Just tell me what happened.”

Silence again.

“Please.” No one could know he said this word. He would kill every demon on hell and earth if they found out he ever said this word.

Castiel looked up at Crowley, puzzled. “Did you just…did you just say please?”

“Don’t mention it.” Crowley sighed. What in the world was he becoming? His friendship with the angel was making him soft. “Seriously, don’t say a thing about it. But really kitten. What went on that has you like this?”

Castiel sighed and stared at the ground, eyes leaking tears onto his nose that eventually would drip off the edge of his nostrils and onto the carpet. It would have been endearing if it wasn’t so pathetic. “He…he said I was dead to him.”

“What?! How come?”

“Because I’m working for you. Because I’m a traitor and a murderer and evil.”

Crowley hissed in a breath. “He said all that?”

“Not in those exact words.”

Crowley looked at the angel, puzzled.

“He said he’d kill me if I ever showed up there again. That he hoped I lived the rest of my life alone.” Castiel sobbed audibly now, tears streaming down his face. “It’s no less than I deserve.”

“You…you deserve?! You gave up your bloody freedom for him!”

Cas looked up at Crowley. “I would never tell him that.”

“You didn’t tell him? He has no clue that the only reason you are in my employ is because I threatened to break Dean into tiny little pieces and you offered up your entire being in exchange?”

“You are correct. He does not know. I will never tell him.”

“You may not ever tell him…” Crowley mumbled to himself, “but I sure will.”

Crowley grabbed the collar of Castiel’s jacket, and the angel didn’t fight him as Crowley pulled him across the room. Well, not until he realized that the demon was chaining him to the wall (with the old cuff he used to tether the angel to the wall with back in the beginning, when he needed the angel to know who held the power.) Then he decided to struggle.

“Let go of me demon!” Castiel screamed, hands trying to pull his collar out of Crowley’s iron grip in an attempt to force the demon to let go.

“Like bloody hell I will.” He pulled on the angel’s ankle and fought off the kicks Castiel was aiming at him, securing the angel to the ankle cuff with relative ease. The poor thing was just too broken to fight with any real power.

Castiel pulled weakly at the shackle, face sad and full of sorrow. “Please, let me go. Do not chain me. I do not know what I have done to anger you, but I promise, I will obey. Just do not bind me.”

Crowley crossed the room to take a last sip of scotch. “I’m not angry with you luv. And I swear, I’ll let you go as soon as I get back. Cross my heart and all that.” Well, if he had a heart he’d cross it. Thought that counts, right?

“Where are you going?” 

“To Casa Singer to knock some sense into that caveman skull of Dean’s.”

Castiel stood and ran to the length of his chain, fighting with all he had to break free. The angel was snarling. “You cannot hurt him! We had a deal!”

Crowley smirked. Angry angel was a welcome change from morose angel. And frankly, the speed of the turnaround was astounding. “Well kitten, if I was planning on hurting him that would be in direct violation of our little agreement. But since I’m only planning on telling him all about you selling yourself to me to save him and his merry band of hunters, not even the tiniest clause of that contract will be violated. So don’t worry your pretty head.”

“No!” The angel was more furious then Crowley had ever seen him, Castiel’s wings flew out in agitation and his body fought to break through the chain so he could throttle Crowley’s throat. His fingers wrapped around the length of silver around his leg, hands pulling in desperation with such force it shook the wall. “Don’t! Leave Dean alone! There is no need to tell him Crowley! Leave him be!”

“Too bad sugar.” The King of Hell was smiling now; face beaming at the angel so angry he was growling, his angelic chest rumbling in hatred. “Don’t break anything before I get back.” And with a last look back at a wrathful Castiel, Crowley disappeared to have a talk with the oldest Winchester.


	11. Chapter 11

Crowley appeared in Bobby’s kitchen a few seconds later. He was a little too familiar with Singer’s rundown shanty for his liking, but as houses go it wasn’t a bad one. He actually had come to respect the crotchety old bastard that owned it, and frankly he liked Bobby. Yeah, he had fixed Bobby’s legs to give them a leg up (haha) with the Apocalypse, but part of him had fixed it because he liked how much of a fighter the son of a bitch is. Yet another thing he could never tell anyone. Add that to his friendship to the angel, and people might think he actually has a heart and gives a damn.

Crowley heard someone in the living room and walked towards it to investigate. As he approached, he could make out Dean Winchester, head in his hands, sniffling on the sofa. Goddammit. Crowley was really getting tired of weeping men.

“Winchester.” 

It was apparent Dean hadn’t heard the demon approach, because he jumped off the couch and reached for Ruby’s knife with his right hand, subtly brushing away tears with his left as he moved towards the table the blade was resting on. “Crowley! What are you doing here?”

“Errands, errands. I won’t be long. Seems you broke my angel, and I need him fixed.”

“I don’t give a shit about you or Castiel. So if I broke your angel, good. Leave me out of it.”

“Oh, believe me, I would love to. I still want to kill you, and having to converse with a creature as idiotic as yourself is torturous. But apparently you upset little Cas, and I need you to kiss and make up.” Crowley waggled his eyebrows suggestively at the hunter. “Figuratively or literally.”

Dean strode forward, brandishing the knife, face contorted in fury. “Kiss and make up? Are you fucking insane? He works for you Crowley! He left my brother and me so that he could work for you! I hope he dies!”

Crowley growled, smirk disappearing at Dean’s harsh words. “Be careful what you say now Winchester.”

“Like I care what you think. You’re the reason he betrayed everyone who cared about him! He broke Sam, he left me and Bobby. All to help you! He’s whored himself out to the King of Hell, and I hope he dies!”

Crowley was across the room in an instant, hitting Dean’s arm and knocking the blade to the ground. Dean tried to push Crowley away, but the demon was quicker, and he tossed the hunter roughly to the floor. As Crowley kicked the knife across the room Dean tried to rise. Crowley swiftly placed his sleek, black, dress shoes on the Winchester’s ribs, his weight keeping Dean down even as he struggled against the demon.

“Always so bloody brash. It’s obnoxious. Now you listen here you idiotic bastard. I went looking for Castiel to get my revenge for his betrayal over the whole purgatory mess. Know where he was? Spying on you to make sure you were safe. So I torture him to make him pay for pissing me off. Physical torture didn’t work, but reminding him of all the times he failed you ripped him apart more than my knife did. And believe me, I cut deep with that bugger.”

“What does this have to do with anything?” Dean said, still squirming underneath Crowley’s foot. “It doesn’t change the fact that he failed everyone who ever gave a damn about him.”

“One, I said listen you baboon. Listening doesn’t involve you interrupting. Two, everyone fails. But he kept trying for you.” Crowley paused to collect his thoughts. “Where was I? Oh yes. So I mention maybe inviting you to our little torture session, and what does he do? Put everything on the table to save your sorry, ungrateful ass. He was willing to give me his grace in exchange for leaving you alone. I decided to take his servitude instead.”

Dean stopped moving underneath Crowley’s foot, and the voice he spoke to Crowley to was much less confident as he said “He…he was willing to give up his grace for me?”

“Oh yes. Though the fool didn’t realize I could take his grace any second since he was all tied up. When I told him as much, he was frantic trying to find something he could give me that I couldn’t already have for myself. So he sold his self to me. Permanent slavery, all for you. Frankly, I think it was a stupid move, but hell, since I came out the winner, who cares? Certainly not you, you motherfucking traitor.”

Dean winced at Crowley’s harsh words and tone. “But he betrayed us by…”

Crowley interrupted, furious again at Dean’s insistence to not let Crowley finish talking. “Oh, shut the hell up! Betrayed you, sure, he did that. But how many times has your dear Yeti done the same? Demon blood, demon whores, killing Lilith. And how many times have you failed your little brother? Let’s see, selling, your soul and making him watch as you went to hell, telling him to never come back after he pissed you off, forcing in his soul when he didn’t want it. I’m sure I’m missing some. And what do you do? You forgive each other! Yet little old good-hearted angel who has no understanding of humanity that would allow him to make the right choices strikes a deal with the devil to save your ass and gets corrupted by power, and you stick your middle finger up at him and tell him to go fuck himself? Quite a double standard luv.”

Dean tried to speak, but Crowley pushed down harder with his boot to force the wind out of Dean's rib cage." I. am. still. talking. Now hear me you bloody oaf. When I leave this house, I am going to talk to Castiel. I will send him here. And you better apologize for what you said to him tonight, so none of this "blah blah blah betrayal" stupidity. Absolutely none. You will tell him he's family and you always forgive family or some other brotherly nonsense you and that green giant of yours always blather on about. If you upset him again, I will come back, take you to the deepest corners of Hell, and make Alistair look like amateur hour. Do we have an understanding?"

Dean nodded. Crowley smiled - the idiot finally got the message on not talking. "Good. I will be seeing you Winchester. Do not cross me again." 

On that warning, the King of Hell disappeared.


	12. Chapter 12

Crowley returned to the apartment, expecting to find a more calm and subdued Castiel. What he found instead was pure fury. Castiel’s wings were still extended, puffed out as if ready for a fight. The angel had destroyed all objects within the reach of his massive wings. Wall hangings lay broken on the floor, the nearby couch was flipped with its cushions lying in disarray around it, and a nearby bookshelf lay sideways with all its tomes strewn out on the ground. Feathers floated in the air in front of Castiel and were gathered around his feet. Cas stood against the wall, continuing to pull at the chain around his ankle and making anguished noises as it continued to hold fast.

“What in the bloody hell is this nonsense?!” Crowley angrily asked, incensed at the abuse his home had endured because of the angel. “I thought I told you NOT to break anything!”

Crowley’s ire was nothing compared to the fire and hate that shown in Cas’ eyes as he turned to confront Crowley.

“If he is dead, I will smite you.” Cas growled. “I will burn your essence with holy flame and turn your body into ash.”

“Oh you will angel? You talk as if you are not currently attached to my wall.”

Castiel fluffed up his wings to their fullest extent, feather tips brushing the high ceiling. “I will break free eventually.” Castiel breathed. “And when I do, I will destroy you.”

Crowley had held the power in his relationship with Castiel for so long, he had forgotten how powerful his angel was. In this moment, Crowley could see the full might of Castiel, and Crowley was imminently grateful that the chain binding Castiel to the wall was currently containing the angel’s fury.

“Never fear feathers.” Crowley said once he had recovered from his moment of fearful awe. “Dean is alive and untouched.”

Castiel began to calm down at this assurance. His wings deflated, and the fire in his eyes calmed to a mere smolder. “Dean is still alive?”

“Well it’s obvious you didn’t listen to a word I said before I left. Look, I told you I wouldn’t violate our contract, and I didn’t. Now will you calm down, or will I need to keep you chained up all evening?”

At that, Castiel fully deflated. “Crowley…I am sorry. I have not been myself.” Castiel slumped against the floor, looking exhausted and defeated. “I have caused such damage. Dean is right. There is truly something wrong with me.” 

Crowley walked over to where Castiel was slumped against the wall so he could comfort the angel. The thought that he was going to go comfort someone was sickening, but he just couldn’t help himself. It was those stupid, sad blue eyes. That was the reason.

“Castiel, I’m the King of Hell. I am an expert when it comes to evil and when it comes to wrong. Hell, I embody all that is wrong. So I know what I’m saying when I tell you there is nothing wrong with you.”

“But Dean…” Castiel protested.

“Dean is a witless ape. And after our little chat, he is willing to apologize for his idiocy.” Crowley pulled a key out of his suit pocket, then leaned over and unlocked the chain around Castiel’s ankle. “You’ll be useless until you go talk to him, so go. Be back at dawn so you can clean up this bloody mess you made.”

Crowley turned and went to sit in his favorite chair in the living room, which had thankfully survived Castiel’s destruction. He needed to put some distance between himself and the only being that seemed to bring out the human parts in him. A small “pop” sound assured him that Castiel had left the room, so he grabbed the remote and turned on news of a war-torn Syria to try and calm his head.


	13. Chapter 13

**Notes for the Chapter:**

> As an update, if everything goes as planned there should be seven more chapters in this work. I'm thinking about making this into a set of related stories, so let me know if there's any interest! And again, thanks so much for reading. Seeing comments and kudos really makes my day :)

Castiel appeared once more in the den of Bobby Singer’s house, even more trepidatious then he had been when he had entered the home earlier that evening. What if Crowley was wrong and Dean didn’t want to apologize? What if Dean tried to kill him? He did say that he would next time he saw Castiel. Maybe he should just go back to Crowley’s and…

“Cas? Is that you?” said a soft voice behind Castiel.

Castiel turned and saw that it was Dean, appearing less wrathful then he had looked earlier in the night. “Dean, I’m sorry. I should not have come and bothered you again. I can go.”

“Cas, look, don’t leave. I’m an idiot and I’m sorry.” Dean ran his hand through his hair anxiously, not looking Castiel in the eye. “Cas, why didn’t you tell me about Crowley?”

“You did not need to know.”

“Cas, I didn’t? You gave up your whole life to save me and Sam, and you didn’t think I needed to know? I screwed up Cas. I shouldn’t have said what I said to you tonight, but I was just so angry after all that purgatory crap.”

“You had every right to be Dean. After what I did to Sam, to the earth, I know I shouldn’t be forgiven.”

Dean walked across the room and laid a hand on Castiel’s shoulder. “Cas, of course you do. You raised me from hell. You fell to help save me and Sam. Hell, you even got ganked by Raphael and Lucifer to try and help us stop the apocalypse. I’m the one that screwed up. I should have trusted you more.”

“Dean, I lost your trust when I worked with Crowley to open purgatory. I should have found another way. I shouldn’t have failed you. I should have…”

Dean stopped Castiel mid-sentence by leaning over and kissing Castiel hard on the mouth. Castiel was too shocked at first to know what to do, but after a few seconds he remembered what he learned from the pizza man and passionately kissed back. Castiel’s right hand threaded through Dean’s hair, and he used his left hand to pull the hunter closer.

Castiel pushed Dean against the wall and continued to kiss him with all of his might. Towards the end of the kiss, Castiel thought that he saw someone in the doorway just out of the corner of his eye. But when he turned to the doorway after Dean broke the kiss, there was no one there.

“Dammit Cas, I really didn’t mean to do that. I just was so happy that you came back after all I said, and I had wanted to do that before the whole purgatory thing, and…well, I just really messed up, didn’t I?”

“Dean, you didn’t mess up.” Castiel said, smiling. “I also have wanted to do that for some time.”

A look of lust flashed across Dean’s face. “Well, I’m more than willing to make up for lost time.”

Castiel looked out the nearby window and sighed. Why did it have to be dawn? “Dean, I would like that. But Crowley said that I must return at dawn, and it is almost daybreak.”

“Will I get to see you sometime soon? I still need to apologize some more for being such an ass.”

Castiel smiled. “I would like that. I will see if I can convince Crowley to allow me to come visit you from time to time.”

Dean looked out the window. “Look, it’s not dawn just yet. Sure you can’t spare a few more minutes?”

Castiel weighed his options for a second. “Perhaps I can stay a little longer.”

Not wanting to waste their remaining few minutes, Dean grabbed Castiel by the collar of his trench coat, pulled the angel over to the couch, and began to make up for lost time.


	14. Chapter 14

How many bottles was it already? Two? Four? Crowley wasn’t sure. He didn’t care. Why wasn’t the bloody alcohol making him oblivious yet? He still remembered what he saw even as drunk as he was, and the pain of it still hurt worse than his best torture implements. Why couldn't he be content with leaving Castiel alone until dawn? But no, he had to go check and make sure a grown bloody angel was safe, and now he can't get the image of Dean and Cas kissing out of his head.

That wanker of an angel always had a thing for Dean. He knew that. But to actually kiss him…he never thought that the angel would have the audacity to make such a move. And Crowley was aware that he told Dean to kiss and make up with Castiel, but he had no idea that Dean would actually listen to him. Frankly, now that he was thinking of it, he would be justified if he killed Dean. He did warn Dean never to cross him again, and frenching the angel was definitely crossing a line.

But really, nothing was stopping Cas from being with Dean. Captivity? Crowley was a sorry captor and they both bloody knew it. His “captive” was currently out past his curfew, snogging one of the Hardy boys for Christ’s sake. 

And why the hell was that? He’s his bloody captive, not his damn roommate. He’d grown too soft and he needed to remedy it. Seemed simplest to start now.

And it would ruin Dean’s night. Perfect.

Crowley took another swig of Craig. “Castiel!” Five seconds. Ten seconds. No response.

Frustrated now, Crowley called out again. “Castiel!!!” Thirty seconds this time; still nothing.

“CASTIEL!!!” Crowley called in anger, slamming his drink on the table, “if you don’t get your angelic arse in here in the next five seconds I will come find you and drag you here myself!”

A flutter of wings entered the room a second later, and a disheveled angel appeared in front of Crowley. “I am sorry Crowley, I…”

“Stow it Castiel. If I wanted your excuses I’d ask for them.”

A look of pain and confusion flashed on the angel’s face. Part of Crowley wanted to comfort the angel and tell him that he was sorry for being cruel. The other part – the part currently in control – didn’t give a damn.

“Crowley, have I offended you?”

“No more of this running around at night” Crowley replied, ignoring the question. “You will either be here or running errands for me. Free time will be spent here. Understood?”

“Yes…” Castiel said, still looking hurt and confused. Something then seemed to dawn on Castiel. “Crowley, I…is this about…”

Crowley grabbed Castiel’s collar and pulled the angel’s face close to his. “If you value your skin angel, I would not complete that sentence.”

Crowley released Castiel’s collar from his grip. “I would also get out of my sight for today. Is that clear?”

Castiel nodded. “Good,” Crowley replied. “Go”. 

Castiel walked out of Crowley’s office, his head down and his body slouched. Crowley almost called Castiel back to apologize, but then the memory of earlier tonight flashed through his mind. Instead, he grabbed his next bottle of Craig and went to work on trying to forget on how much he cared for Castiel.


	15. Chapter 15

**Notes for the Chapter:**

> I'm not in love with this chapter, but I've written on it so many times I just had to let it into the world without being exactly what I was hoping for. I like the next chapter though, so please just bear with me.

“For the love of all things in heaven and hell stop bloody moping!”

Castiel turned around. Crowley had been working on requisition forms, but apparently he was distracted now by Castiel’s moroseness. Castiel hadn’t seen Dean in two weeks and, based on how Crowley reacted the last time he saw Dean, Castiel would never see him again. Castiel was devastated, and had been unable to look anything but sad since the night with Dean.

“I’m not moping. I’m just bored.”

“Bored people don’t have a look on their face like that. You only see that look on the face of someone who has endured pain. Like someone that just got done watching a Dane Cook special."

Castiel ignored the fact that he didn’t know who Dane Cook was. “I’m fine.”

“You’re not fine.”

“Does it matter to you?” Castiel snapped.

“Why wouldn’t it?” Crowley said, hesitantly.

“Because I kissed Dean.”

Crowley froze. “I thought you knew better than to mention that.”

“What did I do wrong?” Castiel asked. “You never told me that I was not to kiss him, or I would not have done so.”

“That’s not the point Castiel.”

“What is the point?” Castiel looked pleadingly at Crowley. “Please, I’m just trying to understand. Everything has changed between you and I since that night, and I wish we could go back to how we were Please.”

Castiel could see the pain of his actions on Crowley's face, and something that looked a lot like concern. But he couldn't understand why - Crowley had no reason to care if Castiel wanted to be with Dean. Although Castiel had grown to think of Crowley as a friend, Castiel wasn't sure that Crowley thought of him as anything but a servant.

“Do you love him?” Crowley whispered.

“I do not know.” Castiel replied, a bit taken aback at the question. “I really don’t. But I care for him. I have for a while.”

Crowley was silent for a few moments. “I…see. Then don’t let it be me that keeps you apart. Leave. You’re free of me.”

Castiel gaped at the demon. “We had a deal. I am to serve you for a lifetime in exchange for the Winchester’s safety.”

“A deal that I will still honor,” said Crowley, face buried in his hands, his voice sounding strained and resigned. “I will leave the Winchester’s and Bobby alone. Your servitude is no longer required.”

Castiel couldn't understand what was happening. He had sold his soul for eternity, but Crowley was freeing him after less than a year? “But Crowley…”

“Are you deaf?!” Crowley's voice abruptly changed as he lifted his face from his hands and snarled at Castiel. “I said leave you bloody idiot. So leave!”

Castiel sat in shock for a few more seconds. He wanted to say something to Crowley, to thank him, to say goodbye, just something. He wanted to know what had changed, why Crowley had decided to let him go. But the wrath on the demon’s face kept Castiel silent. Crowley turned, grabbing his paperwork to get back to work, and by the time he turned back the angel had left.


	16. Chapter 16

It had been a month and a half since Castiel's captivity had ended, and although it should have been a joyous time for the angel, Castiel couldn't help but feel a little empty.

He had been unable to pinpoint why he felt this way. Everything was going swimmingly with the Winchesters. Castiel had been helping them on hunts and was now a valued member of the team. Just today Castiel helped kill a coven of witches in Maine, and Dean was over the moon with happiness. He showed Castiel how happy he was when he pinned the angel to the hotel room wall as soon as they got back. 

"Sam went to the next town over to pick up some grub," Dean whispered in his ear. "We should have the room to ourselves for at least an hour."

Castiel was nervous. Dean had been wanting to move their physical relationship forward, but Castiel kept finding a reason to delay. The first time Dean brought up having sex was during the drive to a hunt in Delaware, and Castiel had needed help to figure out how to delay intimacy with Dean without hurting Dean's feelings. A nice - but for some reason perplexed - gas station attendant had told Castiel that she always told men she had a headache if she didn't want to be physical. Castiel bought Dean's beef jerky, then promptly went to the car to tell Dean that he couldn't possibly be physical right now since he had a headache. Dean didn't bring up the issue again that day, so Castiel kept using the excuse.

"Dean, I would very much like to be intimate with you, but I have a headache."

Dean pulled back from the angel, sadness and frustration written on his face. "Cas, you can stop that. I know you don't have a headache."

"How do you know that?"

"Because in how many years we've known each other you never once mentioned getting a headache. But now it seems that every time I want some alone time with you, you somehow have one." Dean sighed. "Cas, if you don't want to be with me, you can just tell me."

"Dean...It's not that." Castiel said.

Dean went to sit on the bed, passing his fingers through his hair in annoyance. "Isn't it? You haven't been happy since you got here."

"Of course I have Dean! I enjoy being here to help you and your brother."

"That's not what I meant. You seem happy enough to hunt. It's just...like the other day, right? We went in that house and you saw that antique collection. You wanted to talk all about it, but I don't know antiques and Sam only cares about old things if he gets to nerd out about lore. And when I told you that, you got a sad look on your face and said 'Crowley loved to talk about antiques.'" Dean hesitated for a moment. "It's him, isn't it? He's what's absent. You miss him, don't you?"

"I don't know Dean." Castiel replied.

"Come on Cas, I think you do. I know you wanted to be with me before all that purgatory crap, and I think that's why you started this relationship with me, but I think how you felt about me changed once you were taken by Crowley. I think it just took you some time to figure that out."

Castiel moved to sit beside Dean on the bed. He sat in silence for a moment, contemplating what Dean had said. "Perhaps you are right. I would have never...Dean, I care for you. But we are vastly different."

"I know Cas. I should have know it wouldn't work when you said you didn't know what a 'Led Zepplin' was."

"Balloons cannot be made out of lead Dean."

Dean laughed softly at the angel. "As much as I can't stand the bastard, he does seem to care for you. He wouldn't have come and yelled at me for hurting you if he didn't. And he certainly wouldn't have freed you."

Castiel cocked his head to the side, perplexed. "You think that?"

"Yeah, Cas, I do. But you'll need to ask him."

"Dean, I...thank you. I'm sorry if I hurt you."

"Nah, it's okay." Dean smiled. "There's plenty of other fish in the sea. Or, as I like to say, there's plenty of other bar maids to bang."

Castiel smiled. "Friends Dean?"

"Friends, Cas. Now, I can't believe I'm saying it, but go find Crowley and tell him you love him. But come back sometime, alright?"

"I promise I will Dean. Thank you." And with a whoosh sound, Castiel was gone.


	17. Chapter 17

**Summary for the Chapter:**

> Okay, so I'm so sorry this was over a week before updating. Here's why - I am not yet finished with the smut chapter. Like it should not be this hard. It is written mostly, which believe me is an improvement since nothing was written before I started posting. I am hoping to find my muse and finish writing it by the end of this week. Bonus though - I think it will be the longest chapter in this whole tome. So that could be fun. Two chapters to go, so thank you for taking this journey with me. It means so much.

"Untrustworthy, worthless, feckless morons!" Crowley bellowed as he lit the last of the three demons on fire. "And as for the rest of you," Crowley snarled to the remaining two dozen of his top agents who were pressed up against the walls of the throne room to try and avoid his anger, "this is what happens when you fail me. So do not come to me without results and expect to leave this room with your hide. Do you understand, or will I need to roast a few more of you to get it through you thick skulls?!"

"We understand our king" said Barnabas, Crowley's second in command. He was a groveling weasel of a demon, but he was one of the few that Crowley could count on to deliver results.

"Then all of you get out of my sight. And don't return without finishing the tasks I've assigned you." Every demon in the room gave a deep bow and left except Barnabas, who lingered behind, shifting nervously from foot to foot. It seemed that he had something on his mind, and Crowley didn't want to hear it.

"You are included in the 'all of you' group Barnabas"

"Yes my king. It's just, you've roasted eleven demons this month."

"I can bloody count. Get to the point."

Barnabas swallowed, trying to buy himself some time to build up his courage. "Of course your majesty. I only bring it up because, well, it's left a bit of a gap in your command structure. And we're having trouble replacing the ones that we've lost."

Crowley's brow furrowed with anger. "Then. Work. Harder."

"We have my king!" Barnabas grovelled, trying to avoid Crowley's wrath. "But I am just concerned. You have always been a fair leader, and you've always punished incompetence, it's true. But in the last month and a half you have killed more demons than you have in the last year."

"Tread carefully Barnabas," Crowley warned.

Barnabas inhaled deeply then so as to not lose his courage, he blurted out in one breath "Is it because of the angel?"

Crowley slowly rose from his throne and his second fell to his knees in fear. "I told you never to mention him again. Ever."

"I know, I know!" Barnabas replied, looking straight at the ground. "But it seemed that you've been different since he left, my king. If I could only procure him, perhaps..."

"Listen here you ingratiating idiot, if you weren't good at your job then you would be ash as well. So I would get the hell out of this room before I decide to have barbecue Barnabas."

Without another word, Crowley's second-in-command scurried from the room. Crowley sat back down and put his head in his hands. Barnabas was right - things just hadn't been the same since Castiel left. Crowley had been much more volatile, much quicker to punish and unable to forgive even the smallest errors. What had he become that an angel leaving would turn him into an emotional and unstable wreck?

"You know, you didn't have to scare him. He was right."

Crowley's head shot back up. "And just who the hell-"

It was Castiel. 

"It can't be...you're not...he would never have come back."

Castiel walked towards him with a smirk. "Truly Crowley, you and I have lived long enough to know that 'never' doesn't really exist."

Crowley stood and walked slowly towards the angel. "So if it is you, which I'm still not sure it is, why would you return?"

They both continued walking until they were within a foot of each other. "Angels by nature are not sentimental beings. We rarely form attachments. So when I realized that I cared for you, had feelings for you, I had to return. I have not experienced anything like this, and I should have not left you before. Please forgive me for that mistake."

Crowley gaped. "But wait, just wait. You're with Dean."

"I'm not. Dean and I tried, but we never worked. It took a while for me to realize that I only cared for him as a friend. That it's not Dean that I want to be with - it's you."

Crowley stood silent, stunned by the angel's confession. "You want me? Me, your former jailor? Do angels get Stockholm Syndrome?"

Castiel smiled, and closed the distance between the two of them so that his face was just inches from Crowley's. "You and I both know that you were a lousy captor."

"Was not."

"You cared too much for me to be very effective." Crowley grimaced - was he that obvious? "But does that matter? I am here out of my own choice because I care for you, not because I have stock home sydrome."

Crowley laughed at the angel. "Stockholm syndrome, " Crowley corrected. "It's actually a term I helped coin. See, I had this convict come to me in 1973 for a deal, and I told him..."

"You talk too much," Castiel interrupted, and without warning his lips met Crowley's. Crowley was first shocked by the angel's move, but after a few seconds his lust for Cas overwhelmed him. He tangled his fingers through Cas' dark hair with his right hand, and used his left hand to grab Castiel's ass and pull the angel closer. Castiel hummed into Crowley's mouth as their bodies met, and they could both feel each other's arousal. 

After a minute of frenetic kissing, Crowley pulled away with a sigh. "Kitten, I'd love to keep going, but this is the throne room. We could be interrupted at any moment, and although I could turn any demon to ash for so rudely interrupting I probably can't afford the loss. So what say you to taking this to my room?"

"Please Crowley. I need you." Castiel said, his lust causing his voice to be even deeper than normal. And with that, Crowley smashed his lips into Castiel's and transported them both to the bed chambers of the King of Hell.


	18. Chapter 18

**Notes for the Chapter:**

> So again my apologies for taking so long, and thanks for being patient with me. A lot of unexpected stuff happened in my life at once, and now that it's finally calmed down I've been able to finish this chapter. This is my first try at smut, so it's a bit rough. If you have feedback, I'd love to hear it. This is the penultimate chapter to this work, but I'm hoping to do a series of interconnected one-shots after this ends. Look for the final post sometime this week. And thanks again!

In the next moment, both the angel and demon landed together on Crowley's plush bedspread. Castiel fell on top of Crowley, the angel grinding against Crowley's erection while still passionately kissing the demon.

"Crowley," Castiel panted, "You are wearing too many clothes".

Crowley was half-tempted to vanish both their outfits away in an instant. Perhaps somewhere far away like the moon in the hopes that Castiel would eventually give up on finding his bloody trench coat and instead start wearing some half-decent tailored clothing. But he felt that he wanted to savor the moment like a fine glass of Craig, so he resisted the urge to magic away their clothes.

He reached up and undid the angel's tie first, gently untying it and setting it on the nightstand. Next went the trench coat, which Crowley unceremoniously threw to the floor. With his lust becoming more and more intense, Crowley removed Castiel's shirt forcefully and sent a few buttons flying. Truly impatient now, Crowley vanished the rest of their clothing. He couldn't wait for NASA to try and figure out how boxers ended up on the moon rover. 

Castiel was chuckling softly to himself at the demon getting fed up and vanishing their clothing, so Crowley arched up into Castiel to take the smirk off the angel's face.

Castiel growled at the movement, and then began to move against Crowley with greater earnest. They both ground against each other, trying to find relief in the friction the movement created.

Crowley's hands explored Castiel's body, fingers tracing patterns on Castiel's chest as the demon's hands moved slowly lower. As his hands moved further south and closer to Castiel's erection, the angel stopped moving and pulled away slightly.

"Feathers, if you don't want to do this then I won't make you., You're were never that kind of slave," Crowley said, pulling his arm away so as not to make Castiel uncomfortable. 

Castiel pulled back to rest on his haunches so he could get a good look at Crowley's face. "It's not that I don't want this - I very much want this. It's just...I've never done this before and I'm not sure what to do. I mean, I watched the movie with the pizza man, and Dean shared some tips with me, but I don't feel like I know enough to make this good for you."

Crowley sat up and used his right hand to cup Castiel's chin. "I don't need you to be experienced Castiel. You wouldn't be the first virgin I've sullied."

Castiel smiled sheepishly. "So you're alright with me being new at this?"

Crowley used the hand cupping Castiel's chin to pull the angel closer. "Of course I am. As long as you tell me what works for you, and I tell you what works for me, then we'll be fine." Crowley then closed the distance between the two of them and kissed Castiel deeply.

After a couple minutes, Crowley ended the kiss. "Castiel, can I touch you now?" 

"I would like that," Castiel replied. Crowley moved his hand south again, this time firmly grasping Castiel's dick and slowly moving up and down the shaft. Castiel's eyes flew wide, and he began to make whining noises that became louder and more desperate as Crowley continued to move. 

Castiel began thrusting his hips up into Crowley's hand. Crowley could see how worked up the angel was getting, but he didn't want the angel to come too soon, so he removed his hand from Castiel.

"Did that feel good angel?"

It took Castiel a moment to reply. "I have been on this earth for millennia, yet I have never felt anything like that. Now I can see why humans are so fond of sex."

Crowley chuckled. "Demons are a bit fond of it too. It's just you angels that haven't figured out what's pleasurable."

"Perhaps I can bring this knowledge back to my kin."

"Be a missionary about missionary?"

"Again, you're talking to much," Castiel said. 

"Well then I should put my mouth to better use, " Crowley said. He pushed the angel over onto his back, leaned down, and Crowley took all of Castiel's erection into his mouth with one swift movement.

Castiel keened, hips shooting up off the bed as he instinctively tried to move deeper in to Crowley's mouth. Crowley bobbed up and down slowly, trying to make sure that Castiel didn't come too soon. The slow movement was torturous for the angel, who began to moan and pant louder and louder as Crowley continued. 

"Crowley please..."

"Please what?" Crowley said, moving his mouth off Castiel's dick, his lips just barely resting on the tip of Castiel's member.

"I need to touch you, taste you. Please."

"Just make sure not to use your teeth kitten," Crowley stated. Crowley moved to lay back, and Castiel crawled across the bed until his mouth was hovering over Crowley's impressive erection. He looked hesitantly at the size of Crowley, but within a few seconds he gathered his resolve and Castiel took as much of Crowley's length into his mouth as he could. He bobbed up and down, doing his best to imitate what Crowley had done for Castiel just a minute ago.

Crowley had been never gone to heaven, having sold his soul and all, but he imagined heaven couldn't be much better then what he was feeling now. The angel was a bit sloppy and awkward with his movements, but he was rapidly learning and very enthusiastic, and after a few minutes Crowley was keening and moving his hips in time with Castiel's rhythm. 

As his pleasure grew, Crowley became overwhelmed with his need to be inside Castiel. Crowley reached out and began maneuvering Castiel so that his rear was facing Crowley. "Kitten, are you ready for me to be inside you?" Crowley said as his fingers trailed up and down Castiel's ass. The angel hummed his affirmative, and the vibrations felt so good that Crowley shivered. 

Crowley utilized his magic to transport a bottle of lube into his palm, using a generous amount to coat his fingers. Crowley then inserted one finger into Castiel, and the angel bucked at the sensation. "Easy Castiel," Crowley said. "It may feel uncomfortable for a little bit but you'll get used to it."

After giving Castiel enough time to get adjusted, Crowley inserted a second finger into the angel. Cas tried to keep up a steady rhythm while bobbing up and down on Crowley's cock, but the more Crowley thrust his fingers into the angel, the more erratic Castiel's movements became. Crowley needed to get Castiel prepped for the dick Crowley sold his soul for, so it took several minutes and four fingers before Crowley felt comfortable that his girth wouldn't injure the angel.

Finally, Crowley felt Castiel was thoroughly prepped. "I think you're ready feathers."

Castiel slowly moved his lips up and off of Crowley's dick. If there was anything as beautiful as his angel, with pupils blown and Crowley's precum glistening on his lips, Crowley couldn't name it. 

Crowley maneuvered Castiel on top of him. Crowley wanted to look at the angel, see his face as he fell apart, but he also wanted Castiel to be in control the first time. He wanted to ease Cas into it, to not spook him or make things unpleasant. Crowley had many ideas on how he would be the King in bed in the future, but tonight he wanted Castiel to feel safe. Ugh, he was becoming as sentimental as the Winchesters.

Castiel straddled Crowley, hovering over him, his entrance just barely touching Crowley's tip. 

"Slow and steady kitten. I'm in no hurry."

Castiel nodded, and he slowly moved to take Crowley inside him. It was exquisite torture, and he was falling apart with need. 

It seemed Castiel was feeling the same way. His movements started out slow, then hastened little by little as Crowley began to fill him. Finally, his lust overcame him, and Castiel took Crowley's last two inches inside him in one quick movement. Castiel and Crowley both cried out at the same time at the pleasure.

Cas then began moving in earnest, awkwardly at first and then more sure. Crowley had wanted Castiel for awhile, and with this being Castiel's first time, both of them knew that it wouldn't last long. Castiel kept a quick pace, and Crowley guided Castiel's hips with his hands, moving Castiel up and down in a steady rhythm. 

Both held out longer than they expected, trying to please the other. Crowley began thrusting up during Castiel's downward movements, and after several strong thrusts, Castiel came. Crowley was only a few seconds behind - he came undone watching the angel experience such pleasure for a first time.

Sweaty and exhausted, Castiel pried himself off of Crowley and lay down beside the demon. Crowley spooned Cas, pulling him close into him.

Crowley slowly started to drift off to sleep, content in the angel's warmth and still high off endorphins.

As the demon was drifting off, Castiel spoke. "Does this mean that I can stay?"

Crowley leaned his chin on Castiel's shoulder. "I shouldn't have let you leave in the first place. You being my slave and all."

Castiel chuckled, but then sighed.. "You can quit acting Crowley. You're allowed to have feelings."

"Demons aren't supposed to have feelings luv."

Castiel turned over so that he was looking Crowley in the eyes. "You're the King of Hell. You get to set the rules for demons."

Crowley leaned in sleepily, eyes closed as he slowly kissed the angel. "Then I rule that you can stay with me as long as you want. That we're partners this time, that we're equals. And that I will try to make you happy until the end of my reign."

Cas smiled. "Then may you have a long reign, my king."

They both drifted to sleep a few moments later, both more happy and content then they could ever remember being.


	19. Epilogue

Sam adjusted Cas’ blue tie and helped smooth down his always mussed-up hair. “There. That should make you more presentable. And I like the tie.”

“What is the saying…something blue, correct?” Castiel replied. “Crowley told me I should be traditional.”

Dean smirked. “Did he also mention that’s a tradition for brides?”

Castiel pursed his lips in displeasure. “No, he did not. So it is probably unlikely the other traditions he told me about are true. Sam, on wedding nights, when couples copulate, is it traditional…”

Sam sputtered and blushed. “Cas, I can almost guarantee you that any wedding night tradition that Crowley mentioned is not a tradition. And is probably illegal. Anyways, I like the tie. It brings out your eyes.”

Dean laughed. “Dude, you are such a girl.”

“Jerk.”

The door to the dressing room that Cas was changing in opened a crack, and a short frame filled the doorway. “Sorry to break up the reunion show here," Crowley said "but we have a wedding to get to and if you’re finished primping we should probably get on with it.”

Castiel gulped. “Be there in a second.”

“Hurry it up kitten. This place knows I shouldn’t be here. Why you insisted on getting married in a church I will never understand.”

“Mostly to aggravate you.” Castiel replied. Crowley closed the door, grumbling. 

“You ready Cas?” Dean asked.

“I…yes. I’m ready Dean.” 

“Let’s go then.”

**Notes for the Chapter:**

> So that's it! This work was way too many years in the making, but I hope to continue with this story soon. I plan on posting a prequel if you will, something that I wrote a year or two before the main body of this that fits in with the story and would be the very beginning of their relationship together. Once that's posted, I plan on delving into Crowley and Castiel's married life, which I'm excited to do. I'm gonna try my hand at smut again too. So please stay tuned if you liked this story, because I will continue with it. And again, so many thanks for reading. Seeing kudos and comments has kept me going on the days when other things in my life aren't so great. So all my thanks.


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